Captain Benjamin Williams House

The Main Street Historic District encompasses the historic commercial center of Middletown, Connecticut, United States. Middletown was one of the most important ports on the Connecticut River during the colonial period, and Main Street "has been the center of community life since the earliest period of settlement". Today Main Street is home to a number of 19th century buildings, maintaining the bulk of its historic character. It was listed on the National Register of Historic Places in 1983.

Middletown is a city in Middlesex County, Connecticut, United States. Located along the Connecticut River, in the central part of the state, it is 16 miles (26 kilometers) south of Hartford. Middletown is the largest city in the Lower Connecticut River Valley Planning Region. In 1650, it was incorporated by English settlers as a town under its original Native American name, Mattabeseck, after the local Wangunk village of the same name. They were among many tribes along the Atlantic coast who spoke Algonquian languages. The colonists renamed the settlement in 1653. When Hartford County was organized on May 10, 1666, Middletown was included within its boundaries. In 1784, the central settlement was incorporated as a city distinct from the town. Both were included within newly formed Middlesex County in May 1785. In 1923, the City of Middletown was consolidated with the Town, making the city limits extensive. Originally developed as a sailing port and then an industrial center on the Connecticut River, it is now largely residential. Its downtown, based on Main Street, serves as a popular retail, dining, and bar district near Wesleyan University. Middletown was the county seat of Middlesex County from its creation in 1785 until the elimination of county government in 1960. As of the 2020 census, the city had a total population of 47,717. Middletown, Connecticut is considered the southernmost city in the Hartford-Springfield Knowledge Corridor Metropolitan Region, which features a combined metro population of 1.9 million. Middletown is largely a politically progressive city, and is home to one of the largest pride events in all of Connecticut.

The Church of the Holy Trinity is an historic Episcopal church at 381 Main Street in Middletown, Connecticut. Completed in 1874, it is one of the city's finest examples of Gothic Revival architecture. Its nearby former rectory, also known as the Bishop Acheson House, is one of its finest Colonial Revival houses. The two buildings were listed on the National Register of Historic Places in 1979.

The Old Middletown Post Office, in Middletown, Connecticut, also known as the U.S. Post Office, was built in 1916. It was listed on the National Register of Historic Places (NRHP) in 1982. The building is also on the NRHP as a contributing property of the Main Street Historic District.

The Middletown–Portland railroad bridge is a swing truss railroad bridge crossing the Connecticut River and Route 9 in Middletown, Connecticut, just south of the Arrigoni Bridge. The bridge is a Warren through-truss swing bridge with an overall length of 1,142 ft (348 m) and a rotating center span. It is used by the Providence and Worcester Railroad to serve freight customers in Portland.The first rail bridge at the site was constructed by the Boston and New York Air-Line Railroad in 1873. It was replaced by the current bridge in 1911. The bridge was featured prominently in the video for the 1993 Billy Joel hit "The River of Dreams".

O'Rourke's Diner is a diner located in the Main Street Historic District in Middletown, Connecticut.

The Broad Street Historic District encompasses a well-preserved 19th-century residential area in Middletown, Connecticut, USA. Centered on Broad and Pearl Streets west of Main Street, the area was developed residential in response to local economic development intended to revitalize the city, whose port was in decline. The district includes the city's largest concentration of Greek Revival houses, and was listed on the National Register of Historic Places in 1988.

Russell Library is an 1876 library located at 123 Broad Street in Middletown, Connecticut.

Saint Sebastian is a Roman Catholic church in Middletown, Connecticut, part of the Diocese of Norwich.

The Metro South Historic District encompasses a portion of the downtown area of Middletown, Connecticut. Extending south from Main and College Streets for two blocks, this area was developed in the 19th century, and contains a diversity of well-preserved architecture from that period, some with association to locally important individuals. It was listed on the National Register of Historic Places in 1980.

The Arrigoni Bridge, also known locally as the Portland Bridge is a steel through arch bridge carrying Route 66 and Route 17 across the Connecticut River, connecting Middletown, Connecticut, to Portland, Connecticut. When it opened in 1938, the 1,200 feet (370 m) bridge was the most expensive bridge ever built in Connecticut, at a cost of $3.5 million. Its two distinctive 600 feet (180 m) steel arches have the longest span length of any bridge in the state. The bridge has an average daily traffic of 33,600.It was named after state legislator Charles J. Arrigoni, who promoted the project. Arrigoni served in the Connecticut House of Representatives from 1933 to 1936 and in the Connecticut State Senate from 1937 to 1940.

The Middletown, Connecticut Christopher Columbus statue was a memorial to Columbus that was installed in the city's Harbor Park. The sculpture was donated to the city in 1996 by the Italian American Civic Order, the Italian Society of Middletown and local Italian-American families.The statue has been repeatedly vandalized. In 2016 the test on its plinth, reading "discoverer of America" was changed to "looter of America". It was damaged in 2017 when vandals chipped away the sculpture's nose. Also in 2017, vandals painted the statue's hands in red, and left the spray-painted text "kill the colonizer" on the statue's base. In 2019 it was vandalized again with red spray-paint.The statue was removed in June 2020.